Christopher Robin dog sits the neighbor dog Skippy. Skippy only obeys when a toy squeeze horn is used. When Skippy gets dirty and runs away following horn noises, Christopher Robin and his friends must hunt him down and clean him up before the neighbors get home.

Christopher Robin tells his friends not to play with his toy train when his mom needs him, but Tigger decides to play with it anyway. When he loses control of the train, the friends imagine themselves in the Wild West trying to stop the rogue train.

Gopher gets a new shovel, but when he tries to improve everyone's homes, he brings more chaos than help. Piglet remembers that it's Pooh's birthday, so Rabbit and Tigger help him make and decorate a cake for Pooh.